8-Hydroxybergapten

Details

• Internal ID: f7265cfc-aa17-4e1d-b975-b4e8aa426e01
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens > 5-methoxypsoralens
• IUPAC Name: 9-hydroxy-4-methoxyfuro[3,2-g]chromen-7-one
• SMILES (Canonical): COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)O
• SMILES (Isomeric): COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)O
• InChI: InChI=1S/C12H8O5/c1-15-10-6-2-3-8(13)17-12(6)9(14)11-7(10)4-5-16-11/h2-5,14H,1H3
• InChI Key: MVJHUMZXIJPVHV-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₈O₅
• Molecular Weight: 232.19 g/mol
• Exact Mass: 232.03717335 g/mol
• Topological Polar Surface Area (TPSA): 68.90 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 1603-47-0
• 9-Hydroxy-4-methoxypsoralen
• 9-HYDROXY-4-METHOXY-PSORALEN
• 9-hydroxy-4-methoxyfuro[3,2-g]chromen-7-one
• KBZ9E8KHG6
• UNII-KBZ9E8KHG6
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy-4-methoxy-
• CHEMBL1934069
• 7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-4-methoxy-
• 9-Hydroxybergapten
• 9-Hydroxy-5-methoxypsoralen
• 5-Methoxy-8-hydroxy-psoralen
• SCHEMBL6361059
• MVJHUMZXIJPVHV-UHFFFAOYSA-
• C12H8O5
• DTXSID20166854
• CHEBI:174187
• MVJHUMZXIJPVHV-UHFFFAOYSA-N
• BAA60347
• HY-N6010
• BDBM50361383
• AKOS000277887
• MS-23324
• PD158111
• CS-0032148
• FT-0775442
• 9-hydroxy-4-methoxyuro[3,2-g]chromen-7-one
• E88624
• 9-hydroxy-5-methoxy-2H-furo[3,2-g]chromen-2-one
• 4-METHOXY-9-OXIDANYL-FURO(3,2-G)CHROMEN-7-ONE
• 9-Hydroxy-4-methoxy-7H-Furo(3,2-g)(1)benzopyran-7-one
• 9-HYDROXY-4-METHOXY-7H-FURO[3,2-G]CHROMEN-7-ONE
• 9-Hydroxy-4-methoxyfuro[3,2-g][1]benzopyran-7-one, 9CI
• 5-Benzofuranacrylic acid, 6,7-dihydroxy-4-methoxy-, delta-lactone
• InChI=1/C12H8O5/c1-15-10-6-2-3-8(13)17-12(6)9(14)11-7(10)4-5-16-11/h2-5,14H,1H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9827	98.27%
Caco-2	+	0.5943	59.43%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7043	70.43%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9195	91.95%
OATP1B3 inhibitior	+	0.9175	91.75%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9028	90.28%
P-glycoprotein inhibitior	-	0.8558	85.58%
P-glycoprotein substrate	-	0.9115	91.15%
CYP3A4 substrate	-	0.5927	59.27%
CYP2C9 substrate	-	0.8431	84.31%
CYP2D6 substrate	-	0.8139	81.39%
CYP3A4 inhibition	+	0.6791	67.91%
CYP2C9 inhibition	-	0.7069	70.69%
CYP2C19 inhibition	+	0.7217	72.17%
CYP2D6 inhibition	+	0.7682	76.82%
CYP1A2 inhibition	+	0.8969	89.69%
CYP2C8 inhibition	-	0.7890	78.90%
CYP inhibitory promiscuity	-	0.5489	54.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Warning	0.4683	46.83%
Eye corrosion	-	0.9403	94.03%
Eye irritation	-	0.6770	67.70%
Skin irritation	-	0.6053	60.53%
Skin corrosion	-	0.9789	97.89%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6602	66.02%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.8177	81.77%
skin sensitisation	-	0.8631	86.31%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8434	84.34%
Acute Oral Toxicity (c)	III	0.7058	70.58%
Estrogen receptor binding	+	0.8270	82.70%
Androgen receptor binding	+	0.6102	61.02%
Thyroid receptor binding	-	0.5329	53.29%
Glucocorticoid receptor binding	+	0.7892	78.92%
Aromatase binding	+	0.8460	84.60%
PPAR gamma	+	0.8402	84.02%
Honey bee toxicity	-	0.9345	93.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.7930	79.30%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.64%	94.00%
CHEMBL2581	P07339	Cathepsin D	91.60%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.59%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.19%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.61%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	86.98%	91.49%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	86.11%	94.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.71%	89.00%

Plants that contains it

• Alpinia officinarum
• Ammi majus
• Angelica dahurica
• Angelica japonica
• Angelica taiwaniana
• Casimiroa edulis
• Citrus medica
• Esenbeckia berlandieri subsp. litoralis
• Espeletiopsis purpurascens
• Helianthus californicus
• Hornstedtia reticulata
• Imperata cylindrica
• Phlebodium aureum
• Plectranthus hereroensis
• Spiraea prunifolia
• Toddalia asiatica
• Ursinia anthemoides
• Zanthoxylum spinosum

Cross-Links

• PubChem: 3083726
• NPASS: NPC281835
• LOTUS: LTS0086226
• wikiData: Q72483360